5-Fluoro-DMT
{{Short description|Chemical compound}}
{{Use dmy dates|date=January 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477224355
| IUPAC_name = 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
| image = 5-Fluoro-DMT_structure.png
| width = 200px
| tradename =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 22120-36-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 67P3LCN6RM
| PubChem = 2762738
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2043436
| ChEMBL = 1630729
| C=12 | H=15 | F=1 | N=2
| smiles = CN(C)CCC1=CNC2=C1C=C(C=C2)F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BXYDWQABVPBLBU-UHFFFAOYSA-N
}}
5-Fluoro-N,N-dimethyltryptamine (5-fluoro-DMT, 5F-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT.{{cite journal | vauthors = Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ | title = Improved Fischer indole reaction for the preparation of N, N-dimethyltryptamines: Synthesis of L-695,894, a potent 5-HT1D receptor agonist. | journal = The Journal of Organic Chemistry | date = July 1994 | volume = 59 | issue = 13 | pages = 3738–3741 | doi = 10.1021/jo00092a046 }}
It is known to have affinity for and to act as an agonist of the serotonin 5-HT1A and 5-HT2A receptors.{{cite journal | vauthors = Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ | title = A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines | journal = J Biol Chem | volume = 299 | issue = 10 | pages = 105231 | date = October 2023 | pmid = 37690691 | pmc = 10570959 | doi = 10.1016/j.jbc.2023.105231 | doi-access = free | url = }}{{citation | vauthors = Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, Chang L, Gallant J, Press D, Bains JS, Raithatha S, Hagel J, Facchini P | title=Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery | date=10 March 2023 | doi=10.21203/rs.3.rs-2667175/v1 | doi-access=free | url=https://www.researchsquare.com/article/rs-2667175/latest.pdf | access-date=18 March 2025 | page=}} Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist (cf. lisuride), while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.{{cite journal | vauthors = Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE | title = Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 24 | pages = 4701–10 | date = November 2000 | pmid = 11101361 | doi = 10.1021/jm000339w }}{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/S0091-3057(01)00720-1 | s2cid = 6480715 }}
5F-DMT produces a robust head-twitch response in mice, and hence is a putative serotonergic psychedelic.{{cite journal | vauthors = Duan W, Cao D, Wang S, Cheng J | title = Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants | journal = Chem Rev | volume = 124 | issue = 1 | pages = 124–163 | date = January 2024 | pmid = 38033123 | doi = 10.1021/acs.chemrev.3c00375 | url = }}{{cite journal | vauthors = Fumàs B, Nadal-Gratacós N, Pablo-Quesada A, Berzosa X, Camarasa J, Pubill D, Escubedo E, López-Arnau R, Puigseslloses P | title = 5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice | journal = Neuroscience Applied | volume = 3 | pages = 104390 | date = 2024 | doi = 10.1016/j.nsa.2024.104390 | doi-access = free }} In another study however, it failed to substitute for LSD in rodent drug discrimination tests, at least at the assessed doses.{{cite thesis | vauthors = Blair JB | degree = Ph.D. | title=Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine | publisher = Purdue University | via = Purdue e-Pubs | date=August 1997 | url=https://docs.lib.purdue.edu/dissertations/AAI9818919/ | access-date=20 March 2025}}
See also
References
{{reflist}}
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Tryptamines}}
{{DEFAULTSORT:5-Fluoro-Dmt}}
Category:N,N-Dialkyltryptamines